Synthesis of copper catalysts for click chemistry from distillery wastewater using magnetically recoverable bionanoparticles

Kimber, Richard L.; Parmeggiani, Fabio; Joshi, Nimisha; Rakowski, Alexander; Haigh, Sarah J.; Turner, Nicholas J.; Lloyd, Jonathan R.

doi:10.1039/c9gc00270g

Cited by 17 publications

(12 citation statements)

References 33 publications

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“…[50] The classical catalytic system for CuAAC reaction is Cu(II) salts along with a reducing agent (sodium ascorbate), [4,[51][52][53][54][55][56][57] which in situ generate the copper(I) ions and usually show good catalytic efficiency. [58][59][60][61][62][63][64][65] Other catalytic systems include metallic copper, [55,66] copper nanoparticles (NPs), [51,56,62] and so on. [67] During the past years, a variety of scientific and methodological developments have been achieved.…”

Section: Introductionmentioning

confidence: 99%

“…Among them, 1,4‐disubstituted [20] and 1,4,5‐trisubstituted 1,2,3‐triazole derivatives [36] are significant, as they are found in a large number of biologically and pharmaceutically active molecules that have a broad spectrum of properties such as antibacterial, [20,36–39] antiepileptic, [40] antioxidant, [41] antifungal, [42] anticancer agents, [43–47] anti‐HIV, [48–49] and other effects [50] . The classical catalytic system for CuAAC reaction is Cu(II) salts along with a reducing agent (sodium ascorbate), [4,51–57] which in situ generate the copper(I) ions and usually show good catalytic efficiency [58–65] . Other catalytic systems include metallic copper, [55,66] copper nanoparticles (NPs), [51,56,62] and so on [67] …”

Section: Introductionmentioning

confidence: 99%

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Thiol‐Functionalized Cellulose Wrapped Copperoxide as a Green Nano Catalyst for Regiospecific Azide‐Alkyne Cycloaddition Reaction: Application in Rufinamide Synthesis

Selim¹,

Neethu²,

Gowri³

et al. 2021

Asian J Org Chem

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In the past few decades, click chemistry (CuAAC reaction) has seen tremendous development both in terms of catalyst designing and method development because 1,2,3triazoles products have shown enormous applications in various fields. The sought after azide-alkyne cycloaddition reaction catalyzed by smaller-sized (~7 nm) Cu(I/II) oxide nanoparticles (Cu I/II O NPs) supported by thiol-functionalized cellulose provided triazole products in excellent yields (90-98%) with remarkable 1,4-regioselectivity, including the 10 g scale synthesis of a rufinamide drug intermediate. The possible reasons for this exceptional activity are the higher ratio of Cu (I), along with the smaller-sized and homogeneously dispersed colloidal nature of Cu I/II O NPs. Most importantly, the reaction underwent industrially friendly greener conditions such as aqueous medium, room temperature, and no additives, etc., suggesting promising for practical applications. The as-prepared catalyst was recycled and reused up to 5 cycles by simply filtering the precipitate 1,2,3-triazoles products without losing significant activity.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Thiol‐Functionalized Cellulose Wrapped Copperoxide as a Green Nano Catalyst for Regiospecific Azide‐Alkyne Cycloaddition Reaction: Application in Rufinamide Synthesis

Selim¹,

Neethu²,

Gowri³

et al. 2021

Asian J Org Chem

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“…Biomolecules can act as capping agents, limiting nanoparticle aggregation while preventing oxidation with the biomass acting a structural support (Narayanan and Sakthivel, 2010 ; Bennett et al ., 2013 ). Microbial processes can also be controlled during scale‐up to tune nanoparticle properties and in some cases can convert metal waste streams to a valuable end‐product, underpinning a transition towards a circular economy (Byrne et al ., 2011 ; Byrne et al ., 2015 ; Kimber et al ., 2019 ). The ability of microorganisms to produce highly active monometallic catalysts is well known (De Windt et al ., 2005 ; Lloyd et al ., 2011 ; Kimber et al ., 2018 ).…”

Section: Introductionmentioning

confidence: 99%

Biotechnological synthesis of Pd/Ag and Pd/Au nanoparticles for enhanced Suzuki–Miyaura cross‐coupling activity

Kimber

Parmeggiani

Neill

et al. 2021

Microbial Biotechnology

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Bimetallic nanoparticle catalysts have attracted considerable attention due to their unique chemical and physical properties. The ability of metal-reducing bacteria to produce highly catalytically active monometallic nanoparticles is well known; however, the properties and catalytic activity of bimetallic nanoparticles synthesized with these organisms is not well understood. Here, we report the one-pot biosynthesis of Pd/Ag (bio-Pd/Ag) and Pd/Au (bio-Pd/ Au) nanoparticles using the metal-reducing bacterium, Shewanella oneidensis, under mild conditions. Energy dispersive X-ray analyses performed using scanning transmission electron microscopy (STEM) revealed the presence of both metals (Pd/Ag or Pd/Au) in the biosynthesized nanoparticles. X-ray absorption near-edge spectroscopy (XANES) suggested a significant contribution from Pd(0) and Pd (II) in both bio-Pd/Ag and bio-Pd/Au, with Ag and Au existing predominately as their metallic forms. Extended X-ray absorption fine-structure spectroscopy (EXAFS) supported the presence of multiple Pd species in bio-Pd/Ag and bio-Pd/Au, as inferred from Pd-Pd, Pd-O and Pd-S shells. Both bio-Pd/Ag and bio-Pd/Au demonstrated greatly enhanced catalytic activity towards Suzuki-Miyaura cross-coupling compared to a monometallic Pd catalyst, with bio-Pd/Ag significantly outperforming the others. The catalysts were very versatile, tolerating a wide range of substituents. This work demonstrates a green synthesis method for novel bimetallic nanoparticles that display significantly enhanced catalytic activity compared to their monometallic counterparts.

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“…Just for retaining the adhesion of phenolic hydroxyl groups, it is better for the grafting reaction to act between the double bonds of cardanol and the MSN, so the MSN must be modified by the silane coupling agent with the sulfhydryl group. Compared to free radical addition reactions, click chemical reaction is one of the most useful and attractive synthetic concepts because of its advantages, such as highly yield and selectivity, simple operation, fast reaction process, moderate reaction condition, and atom economy. , These advantages will ensure that the surface of the MSN is coated with enough cardanol.…”

Section: Introductionmentioning

confidence: 99%

“…Compared to free radical addition reactions, click chemical reaction is one of the most useful and attractive synthetic concepts because of its advantages, such as highly yield and selectivity, simple operation, fast reaction process, moderate reaction condition, and atom economy. 28,29 These advantages will ensure that the surface of the MSN is coated with enough cardanol.…”

Section: Introductionmentioning

confidence: 99%

Click-Grafting of Cardanol onto Mesoporous Silica/Silver Janus Particles for Enhanced Hemostatic and Antibacterial Performance

Chen

et al. 2020

ACS Appl. Bio Mater.

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Janus particles with obvious chemical compartition can perform their functions independently, so they have attracted much attention in biomedical materials. Herein, a mesoporous silica/silver Janus nanoparticle modified with cardanol (C-MSN@Ag) was designed and synthesized via redox and click chemical reactions and was further evaluated as a highly efficient hemostatic dressing. This Janus structure endowed C-MSN@Ag with both prominent hemostatic and antibacterial performance. The hemostatic time of C-MSN@Ag on rat liver laceration was up to 40% shorter than that of MSN and MSN@Ag because of adhesion of phenolic compounds on the tissue and the blocking effect of the hydrophobic alkyl chains from cardanol. Besides, C-MSN@Ag could promote coagulation by forming a three-dimensional network with fibrin more quickly than MSN and MSN@Ag. Additionally, due to the released silver ions and phenolic hydroxyl groups of cardanol, C-MSN@Ag exhibited a broad-spectrum antibacterial rate (∼99%) against both Escherichia coli and Staphylococcus aureus. C-MSN@Ag also possessed non-cytotoxicity. This work not only provides a way for the fabrication of silica-based Janus hemostatic agents by the atom-economical click reaction but also gives a direction for the application of the sustainable naturally occurring cardanol.

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Synthesis of copper catalysts for click chemistry from distillery wastewater using magnetically recoverable bionanoparticles

Abstract: Biogenic magnetite nanoparticles were employed to recover copper from whisky distillery wastewaters, generating an efficient and reusable click chemistry catalyst.

Cited by 17 publications

References 33 publications

Thiol‐Functionalized Cellulose Wrapped Copperoxide as a Green Nano Catalyst for Regiospecific Azide‐Alkyne Cycloaddition Reaction: Application in Rufinamide Synthesis

Thiol‐Functionalized Cellulose Wrapped Copperoxide as a Green Nano Catalyst for Regiospecific Azide‐Alkyne Cycloaddition Reaction: Application in Rufinamide Synthesis

Biotechnological synthesis of Pd/Ag and Pd/Au nanoparticles for enhanced Suzuki–Miyaura cross‐coupling activity

Click-Grafting of Cardanol onto Mesoporous Silica/Silver Janus Particles for Enhanced Hemostatic and Antibacterial Performance

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